Amicoumacin A

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Category Antibiotics
Catalog number BBF-00670
CAS 56592-30-4
Molecular Weight 423.46
Molecular Formula C20H29N3O7

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It is produced by the strain of Bacillus pumilus BN-103. It has anti-gram-positive bacterial activity and can inhibit foot paw edema (inflammation) caused by carrageenan in rats, which is similar to Phenylbutazone, and has a stronger effect on preventing gastric ulcer in rats than Sulpiride.


Related CAS 78654-44-1 (free base)
Synonyms Antibiotic BN 103; (3S)-3alpha-[(S)-1-[[(2S,3S,4S)-1,6-Dioxo-2,3-dihydroxy-4,6-diaminohexyl]amino]-3-methylbutyl]-8-hydroxy-3,4-dihydro-1H-2-benzopyran-1-one
IUPAC Name (2S,3S,4S)-4-amino-2,3-dihydroxy-N-[(1S)-1-[(3S)-8-hydroxy-1-oxo-3,4-dihydroisochromen-3-yl]-3-methylbutyl]hexanediamide
Canonical SMILES CC(C)CC(C1CC2=C(C(=CC=C2)O)C(=O)O1)NC(=O)C(C(C(CC(=O)N)N)O)O
InChI InChI=1S/C20H29N3O7/c1-9(2)6-12(23-19(28)18(27)17(26)11(21)8-15(22)25)14-7-10-4-3-5-13(24)16(10)20(29)30-14/h3-5,9,11-12,14,17-18,24,26-27H,6-8,21H2,1-2H3,(H2,22,25)(H,23,28)/t11-,12-,14-,17-,18-/m0/s1


Antibiotic Activity Spectrum Gram-positive bacteria
Boiling Point 859.6 °C at 760 mmHg
Density 1.351 g/cm3
Solubility Soluble in Methanol

Reference Reading

1. Deep Functional Profiling of Wild Animal Microbiomes Reveals Probiotic Bacillus pumilus Strains with a Common Biosynthetic Fingerprint
Margarita N Baranova, Arsen M Kudzhaev, Yuliana A Mokrushina, Vladislav V Babenko, Maria A Kornienko, Maja V Malakhova, Victor G Yudin, Maria P Rubtsova, Arthur Zalevsky, Olga A Belozerova, Sergey Kovalchuk, Yuriy N Zhuravlev, Elena N Ilina, Alexander G Gabibov, Ivan V Smirnov, Stanislav S Terekhov Int J Mol Sci. 2022 Jan 21;23(3):1168. doi: 10.3390/ijms23031168.
The biodiversity of microorganisms is maintained by intricate nets of interactions between competing species. Impaired functionality of human microbiomes correlates with their reduced biodiversity originating from aseptic environmental conditions and antibiotic use. Microbiomes of wild animals are free of these selective pressures. Microbiota provides a protecting shield from invasion by pathogens in the wild, outcompeting their growth in specific ecological niches. We applied ultrahigh-throughput microfluidic technologies for functional profiling of microbiomes of wild animals, including the skin beetle, Siberian lynx, common raccoon dog, and East Siberian brown bear. Single-cell screening of the most efficient killers of the common human pathogen Staphylococcus aureus resulted in repeated isolation of Bacillus pumilus strains. While isolated strains had different phenotypes, all of them displayed a similar set of biosynthetic gene clusters (BGCs) encoding antibiotic amicoumacin, siderophore bacillibactin, and putative analogs of antimicrobials including bacilysin, surfactin, desferrioxamine, and class IId cyclical bacteriocin. Amicoumacin A (Ami) was identified as a major antibacterial metabolite of these strains mediating their antagonistic activity. Genome mining indicates that Ami BGCs with this architecture subdivide into three distinct families, characteristic of the B. pumilus, B. subtilis, and Paenibacillus species. While Ami itself displays mediocre activity against the majority of Gram-negative bacteria, isolated B. pumilus strains efficiently inhibit the growth of both Gram-positive S. aureus and Gram-negative E. coli in coculture. We believe that the expanded antagonistic activity spectrum of Ami-producing B. pumilus can be attributed to the metabolomic profile predetermined by their biosynthetic fingerprint. Ultrahigh-throughput isolation of natural probiotic strains from wild animal microbiomes, as well as their metabolic reprogramming, opens up a new avenue for pathogen control and microbiome remodeling in the food industry, agriculture, and healthcare.
2. Asymmetric Total Synthesis of Hetiamacins A-F
Gang Wu, Ting Wang, Zhongke Jiang, Shaowei Liu, Chenghang Sun ACS Omega. 2021 Mar 17;6(12):8239-8245. doi: 10.1021/acsomega.0c06267. eCollection 2021 Mar 30.
Herein, we report a concise and stereoselective approach for the asymmetric total synthesis of hetiamacins A-F on the basis of the total synthesis of amicoumacin C, which could be synthesized from a known l-aspartic acid derivative. The synthesis of hetiamacin A was accomplished by an 11-step sequence that featured 1,3-oxazinane ring formation of amicoumacin B followed by amidation in one pot. Hetiamacins B-F were synthesized from amicoumacin A in only one step.
3. Multifaceted Mechanism of Amicoumacin A Inhibition of Bacterial Translation
Elena M Maksimova, Daria S Vinogradova, Ilya A Osterman, Pavel S Kasatsky, Oleg S Nikonov, Pohl Milón, Olga A Dontsova, Petr V Sergiev, Alena Paleskava, Andrey L Konevega Front Microbiol. 2021 Feb 12;12:618857. doi: 10.3389/fmicb.2021.618857. eCollection 2021.
Amicoumacin A (Ami) halts bacterial growth by inhibiting the ribosome during translation. The Ami binding site locates in the vicinity of the E-site codon of mRNA. However, Ami does not clash with mRNA, rather stabilizes it, which is relatively unusual and implies a unique way of translation inhibition. In this work, we performed a kinetic and thermodynamic investigation of Ami influence on the main steps of polypeptide synthesis. We show that Ami reduces the rate of the functional canonical 70S initiation complex (IC) formation by 30-fold. Additionally, our results indicate that Ami promotes the formation of erroneous 30S ICs; however, IF3 prevents them from progressing towards translation initiation. During early elongation steps, Ami does not compromise EF-Tu-dependent A-site binding or peptide bond formation. On the other hand, Ami reduces the rate of peptidyl-tRNA movement from the A to the P site and significantly decreases the amount of the ribosomes capable of polypeptide synthesis. Our data indicate that Ami progressively decreases the activity of translating ribosomes that may appear to be the main inhibitory mechanism of Ami. Indeed, the use of EF-G mutants that confer resistance to Ami (G542V, G581A, or ins544V) leads to a complete restoration of the ribosome functionality. It is possible that the changes in translocation induced by EF-G mutants compensate for the activity loss caused by Ami.

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40

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